Hindered phenyl esters of cyclic borates and lubricants containing same

Abstract

New reaction products obtained by reacting (1) a hindered phenol, (2) a borating agent and (3) a hydrocarbyl carboxylate are described. The preferred reaction sequence involves, first, the reaction of (1) and (2), then reacting the product obtained with the hydrocarbyl carboxylate. Also described are lubricant or liquid fuel compositions containing a major proportion of lubricant or fuel and an antifriction, anticorrosion or fuel reducing amount of the reaction product of this invention and a method of reducing fuel consumption in an internal combustion engine by lubricating the engine therewith.

We claim: 
     
       1. A reaction product prepared by reacting (1) a hindered phenol of the formula ##STR3## wherein R 1  is a C 1  to C 30  hydrocarbyl group and R 2  and R 3  are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula   (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y     where R, Y and Z are selected from the group consisting of hydrogen and a C 1  to C 6  alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula     R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t     wherein R 4  is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5  is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.   
     
     
       2. The product of claim 1 wherein said alkyl groups are tertiary alkyl groups. 
     
     
       3. The product of claim 1 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl. 
     
     
       4. The product of claim 1 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the carboxylate ester is glycerol monooleate. 
     
     
       5. A lubricant or liquid fuel composition comprising a major amount of a lubricating oil or grease therefrom or of a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR4## wherein R 1  is a C 1  to C 30  hydrocarbyl group and R 2  and R 3  are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula   (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y     were R, Y and Z are selected from the group consisting of hydrogen and a C 1  to C 6  alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula     R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t     wherein R 4  is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5  is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.   
     
     
       6. The composition of claim 5 wherein said alkyl groups are tertiary alkyl groups. 
     
     
       7. The composition of claim 5 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl. 
     
     
       8. The composition of claim 5 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compond is boric acid and the carboxylate ester is glycerol monooleate. 
     
     
       9. The composition of claim 5 wherein said lubricant is (1) a mineral lubricating oil, (2) a synthetic lubricating oil or mixtures thereof, (3) mixtures of (1) and (2) and (4) a grease from any of (1), (2) and (3). 
     
     
       10. The composition of claim 9 wherein the lubricating oil is a mineral oil. 
     
     
       11. The composition of claim 9 wherein the lubricating oil is a synthetic oil. 
     
     
       12. The composition of claim 9 wherein the synthetic lubricating oil is a mixture of synthetic oils. 
     
     
       13. The composition of claim 9 wherein the lubricating oil is a mixture of (1) synthetic oil, or mixtures of synthetic oils, and (2) mineral oil. 
     
     
       14. The composition of claim 9 wherein the lubricant is a grease. 
     
     
       15. The composition of claim 5 wherein the liquid fuel is a liquid hydrocarbon or a liquid alcohol fuel, or mixtures thereof. 
     
     
       16. A method of reducing fuel consumption in an internal combustion engine which comprises lubricating and/or fueling said engine with a composition comprising a major amount of a lubricating oil or grease therefrom or a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR5## wherein R 1  is a C 1  to C 30  hydrocarbyl group and R 2  and R 3   are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula   (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y     where R, Y and Z are selected from the group consisting of hydrogen and a C 1  to C 6  alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula     R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t     wherein R 4  is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5  is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.   
     
     
       17. The method of claim 16 wherein said alkyl groups are tertiary alkyl groups. 
     
     
       18. The method of claim 16 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl. 
     
     
       19. The method of claim 16 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the carboxylate ester is glycerol monooleate. 
     
     
       20. The method of claim 16 wherein said lubricant is (1) a mineral lubricating oil, (2) a synthetic lubricating oil or mixtures thereof, (3) mixtures of (1) and (2) and (4) a grease from any of (1), (2) and (3) and the liquid fuel is a liquid hydrocarbon a liquid alcohol fuel or mixtures thereof. 
     
     
       21. The composition of claim 5 containing additionally one or more additives selected from the group consisting of metal phenates, metal sulfonates, zinc phosphorodithioates, polymeric detergents and silicone defoamants. 
     
     
       22. The product of claim 1 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate. 
     
     
       23. The composition of claim 5 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate. 
     
     
       24. The method of claim 16 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate.